Mastering the art of storytelling to drive change.

The Uber-Chicagoan

MEDIUM, 10 / 29 / 2019

The Cubs-themed floor mats — lined by blue track lights — are the first thing you notice inside Santiago’s Honda Odyssey.

Next thing you see is the Chicago Bears flag proudly unfurled from the back of his seat.

Look closer at the driver and you see he’s got a Bears shirt on. Look up and The Blues Brothers is playing on the overhead screen.

They’re all conversation-starters on their own, but together, they’re the start of a Chicago conversation.

“North-sider, huh, guy?”

“Name’s Santiago. Yeah, I grew up in Wrigleyville. Got a World Series video up here, too.”

“So, if a Sox fan climbs aboard and starts squawkin’ South Side, whadya tell ‘em?”

“Hey, it’s good for the city!”

“Not bad. You could be in politics.”

“But if they say the Cubbies suck, I tell them I’ve got a roof rack!”

“Ha!… Thoughts on Joe Maddon?”

“I think he should have stayed. Given him a couple more years. I mean, four out of the five years he was here, we were in the playoffs!”

Agree. Then Santiago asks me if I saw his beads. He points to them — but he’s really undersold the attraction. They’re kelly green beads that actually form a novelty necktie. He wears it every St. Paddy’s day.

“I’m Puerto Rican Irish. My mom’s Irish from Chicago, and my Dad’s from San Juan, so I got the Puerto Rican flag.”

And he does, just to the right of the green tie and Cubs ribbon hangin’ off of the mirror.

All of this paraphernalia likely had a different home a few years ago. Santiago used to drive big rigs all over the country. He had to stop after he took a fall at his house and busted his wrist in nine places.

“I got a titanium plate right here. Made it too tough to shift and to climb in and out of the semi. But I love driving Uber. I don’t miss trucking. I was never home!”

Santiago has a wife and kids in Chicago — his youngest are 33-year-old twins.

After two and a half years crisscrossing Chicagoland in his Odyssey, he’s made good on more than 10,000 trips.

“Ten thousand, three hundred as of this morning. That’s a lot!”

I take his word for it. But later on I check it out. He’s right. Helluva lot of rides. I wonder if he’s always in this good a mood. Seems like it. Seems like he wants to be.

“Ok, last question: what happens if you get a finicky passenger who doesn’t want to watch Jake and Elwood or the Cubs?”

“Well, it’s football season now, so, I’ve got Super Bowl XX to play.”

Of course he does. Santiago is Chicago.